GRACE BAILEY has the space to relax and the size to offer smooth sailing. This makes her a fun and comfortable sailboat for couples, families, and charter groups.
Aboard our schooner is THE way to explore the best of Maine’s rugged beauty. This bold, new perspective makes our trips different. These trips stand out. You will remember them for the rest of your life. We guarantee it.
- Captain Sam Sikkema and Suzannah Smith
Max. Guests
25
Length on Deck
80’
Length Overall
118’
Homeport
Rockland, Maine
Built-In
1882, Patchogue, New York
Grace Bailey Reservations:
(207) 691-9521
| Dates | Length | Price /person |
||
|---|---|---|---|---|
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $2105 | WoodenBoat Rendez-Vous | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1550 | Four night adventure | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $1375 | Long weekend adventure | Learn More |
|
September 29–October 3, 2026 Tuesday to Saturday |
4 nights | $1450 | Fall Foilage Four night adventure | Learn More |
|
June 6–10, 2027 Sunday to Thursday |
4 nights | $1240 | Four Night Adventure | Learn More |
|
June 11–16, 2027 Friday to Wednesday |
5 nights | $1600 | Windjammer Gam | Learn More |
|
June 18–24, 2027 Friday to Thursday |
6 nights | $1750 | Six Night Adventure | Learn More |
|
June 25–28, 2027 Friday to Monday |
3 nights | $1240 | Long Weekend Adventure | Learn More |
|
June 29–July 3, 2027 Tuesday to Saturday |
4 nights | $1450 | Four Night Adventure | Learn More |
|
July 4–10, 2027 Sunday to Saturday |
6 nights | $2165 | Great Schooner Race | Learn More |
|
July 11–17, 2027 Sunday to Saturday |
6 nights | $2165 | Six Night Unplugged Adventure | Learn More |
|
July 18–22, 2027 Sunday to Thursday |
4 nights | $1705 | Four Night Adventure | Learn More |
|
July 23–26, 2027 Friday to Monday |
3 nights | $1530 | Long Weekend Adventure | Learn More |
|
July 27–31, 2027 Tuesday to Saturday |
4 nights | $1705 | Camden Classics Regatta | Learn More |
|
August 1–7, 2027 Sunday to Saturday |
6 nights | $2265 | Swan's Island Music Festival | Learn More |
|
August 8–14, 2027 Sunday to Saturday |
6 nights | $2265 | Six Night Adventure | Learn More |
|
August 15–19, 2027 Sunday to Thursday |
4 nights | $1705 | Four Night Adventure | Learn More |
|
August 20–23, 2027 Friday to Monday |
3 nights | $1530 | Long Weekend Adventure | Learn More |
|
August 24–30, 2027 Tuesday to Monday |
6 nights | $2105 | Six Night Adventure | Learn More |
|
August 31–September 4, 2027 Tuesday to Saturday |
4 nights | $1705 | Camden Windjammer Festival | Learn More |
|
September 5–11, 2027 Sunday to Saturday |
6 nights | $2105 | Sailing & Music w/Mike & Amy Aiken | Learn More |
|
September 12–18, 2027 Sunday to Saturday |
6 nights | $2105 | WoodenBoat Rendezvous | Learn More |
|
September 19–23, 2027 Sunday to Thursday |
4 nights | $1550 | Four Night Adventure | Learn More |
|
September 24–27, 2027 Friday to Monday |
3 nights | $1375 | Long Weekend Adventure | Learn More |
|
September 28–October 2, 2027 Tuesday to Saturday |
4 nights | $1450 | Fall Foliage Four Night Adventure | Learn More |
Stay in the Know
With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!
Monthly Newsletter SignupBrochures
You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.
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